These startups’ success stories will inspire you as they overcame huge obstacles before becoming household names.
If you’re a struggling founder thinking about throwing in the towel… Let’s look at some examples of startup founders who survived tough times to keep going and build household names.
If there’s one startup success story that epitomizes perseverance and creativity, it’s Airbnb. In 2007, founders Brian Chesky and Joe Gebbia couldn’t pay the rent on their San Francisco apartment.
So they came up with the idea of renting out air mattresses and making some money hosting “Air Bed and Breakfasts.” They launched a basic website, but at first they struggled to get traction. As Gebbia recalls:
«In the first 6-8 months we had 5-10 reservations at $80 each.»
Penniless and down to their last $1,000, the founders thought about quitting many times. But they changed their focus, improved their website, gained the trust of hosts, and launched an aggressive marketing effort. According to Chesky:
“On two occasions we were close to throwing in the towel”.
Their big breakthrough came in 2008, when they traveled to Denver to redesign their website and business based on feedback from hosts. By May 2009, they had raised their first round of funding of $400,000.
From those humble beginnings, Airbnb is now worth nearly $100 billion. It’s a true testament to the startup mentality of continually iterating, persevering in the face of challenges, and never giving up.
As Chesky said: “It took us 1,000 days to book our first 500,000 nights… and just 1 last night to book another 500,000.”.
The most important thing: Stay strong despite early rejections and failures. Keep improving your product and your approach until you get traction.
The founders of online payments company Stripe have faced an onslaught of “no’s” over the years. Patrick and John Collison first tried to pitch their idea to people in Silicon Valley in 2010, but were repeatedly rejected. As Patrick later reflected:
“In total, we were rejected by about 25 or 26 investors. “No” was the resounding answer we received from all of them. We were very stubborn.”
What was the main response?
The payments industry was too difficult, over-regulated and over-saturated with big companies for two small-time Irish brothers with no industry experience to disrupt. As one Sequoia Capital investor told them:
There are so many negatives against payments, it’s hard not to look stupid saying yes.
But the Collisons didn’t take no for an answer. They raised a small seed funding from angels, and in 2011, launched their developer-friendly payments system, making it easy to integrate payments into any website. Within two years, companies like Lyft, Reddit, Kickstarter, and thousands more were using their payments API.
Today, Stripe is valued at $65 billion, making it one of the largest fintech companies in the world. Those relentless founders turned all those initial “nos” into a resounding “yes” through perseverance and an undeniably great product.
Key Takeaway: Don’t let rejection from investors or naysayers dissuade you from pursuing a great idea. If you truly believe in the solution, prove them wrong through execution.
Pinterest’s founders had a clear vision from the beginning: Create a visual bookmarking tool that allows people to curate, collect, collaborate on, and get inspired by images from all over the internet.
At a time when most social media was text-based, its early team focused on building a purely visual product. This confused investors, who didn’t understand the appeal of “just pinning images.” The founders were rejected by “pretty much every investor we tried it with in the beginning,” co-founder Ben Silbermann recalls.
One of the first meetings with an investor was particularly brutal:
“I don’t understand, they’re crazy.”
But the founders remained steadfast in their belief that visual discovery was a huge, underserved opportunity.
At first, they scrambled to manually select and upload images to showcase their vision. And while user growth was slow at first, their product began to gain a cult following among hobbyists and special interest groups who loved the visual format and curability.
When the founders simplified the interface and added features like Pinterest boards and the ability to pin from websites, growth began to accelerate rapidly. By 2012, just two years after its launch, Pinterest had broken into the top 20 social networks and had more than 10 million users.
Today, Pinterest has a market valuation of $30 billion. It is the ultimate example of sticking to a product vision from the beginning and not wavering, despite initial skepticism and slow growth.
Key takeaway: Believe deeply in your vision, find a loving audience early on, and stay committed to delivering that core value as you gain traction.
Buzzfeed redefined digital publishing in many ways, thanks to its unique approach to viral content, bold experimentation on new platforms, and heavy reliance on data to make decisions. But getting there wasn’t easy.
The company was founded in 2006 as a kind of viral laboratory where all kinds of experiments were tested with content. In the words of its co-founder, Jonah Peretti:
“We tried everything to go viral: funny websites, batting stance analysis, zombie bites, you name it.”
For years, Buzzfeed struggled to generate revenue and gain legitimacy in the eyes of advertisers. In 2011, five years later, Peretti admitted that they were on the verge of bankruptcy after running out of funding. They managed to raise another $15 million to pivot aggressively and become a true media company.
With the new investment, they increased their content staff and expanded into more original reporting and video. The team constantly analyzed what content resonated best with readers and set about developing more shareable and engaging content in those areas.
This strategic shift paid off, and Buzzfeed’s popularity skyrocketed. Their proprietary data allowed them to seamlessly match advertisers with desired audiences at scale.
Although they faced many problems with their business model in recent years, Buzzfeed’s perseverance and willingness to evolve allowed them to crack the code of creating highly viral and shareable content. At its peak in the mid-2010s, it was one of the most powerful publishers on the internet. Today they are valued at over $75 million.
Key takeaway: Be willing to constantly experiment and evolve based on audience signals and data. A single pivot can transform your trajectory.
In 2009, Alan Schaaf created a basic image hosting service called Imgur as a fun side project while studying computer science at Ohio State University. He created it between classes with no grand ambitions, simply because he wanted an easier way to share images online.
His classmates soon took an interest in the tool, which made posting images on sites like Reddit much simpler. Word spread through online communities, and before Schaaf knew it, Imgur had become one of the most popular image hosting services on the Internet.
A year after its launch, Imgur was getting 300 million monthly visitors through organic growth and referrals alone. As an overwhelmed Schaaf would later recall:
“When I started Imgur, I had no aspirations for it to become a company or anything like that.”
But the founder soon realized he had something bigger on his plate. With the support of the Imgur community, he decided to abandon it and turn it into a real company in 2010. The decision paid off.
Today, Imgur is one of the most beloved and iconic brands on the internet. The company has raised over $60 million in venture funding and employs over 80 people.
With over 300 million monthly users at its peak, Imgur has become a massive community and platform for sharing memes, reactions, viral images, and more.
Not bad for a random university project that took off thanks to the power of word of mouth and the use of internet culture. Here’s how Schaaf sums it up: “When you find something that resonates with people, growth takes on a life of its own.”
Key takeaway: Sometimes the biggest opportunities come from simple ideas and side projects. If you create something that really resonates with your audience, be willing to turn it into a legitimate business.
While each of these stories is unique, these startups share some common themes:
- Perseverance despite rejection and doubts.
- Sticking to your core vision despite skeptics
- Continuous iteration and evolution based on user feedback
- Never give up in the face of extreme adversity.
As statistics show, around 90% of startups end up failing. Many of the most successful startups that we know today as giants were rejected dozens of times and were on the verge of going under before they got back on track.
Take Airbnb, for example, which maxed out all its credit cards and considered quitting many times before finding the right product-market fit.
Or Stripe, which was repeatedly told that the payments industry was impossible for two people outside the company.
Or that the founders of Pinterest laughed at them for focusing on such a seemingly trivial product.
These stories prove that with enough determination, creativity, and a focus on serving users, startups can defy the odds and go from being an underdog to becoming a household name.
The path of startups is never easy, but those who overcome difficulties are the ones who achieve stratospheric success.
